The High Cost of Chasing: Hiring, Selling, and Investing with Clarity
If you don’t know who is right for you, you’re just chasing. And chasing is expensive.
This isn’t just about hiring. It applies to selling, investing, and any high-stakes decision. Because at the core, all of these are the same game, just with different players.
Yet, time and time again, I see founders, sales leaders, and investors making the same costly mistake. They make decisions on gut feel, surface-level impressions, or someone else’s definition of success instead of having a clear, repeatable process.
I recently sat down with powerhouse CEO Stacy Havener on Billion Dollar Backstory to dig into why this keeps happening and, more importantly, how to stop it.
The Hiring, Selling, and Investing Trap: Why Founders Keep Getting Stuck
Too often, founders and CEOs step into hiring, sales, or investment decisions with an “I’ll know it when I see it” mindset. On the surface, this feels intuitive. You have built a business, you have hired before, and you have sold deals, so naturally, you think you will recognize the right fit when it is in front of you.
Except, that is rarely how it plays out.
When you do not start with clarity, you:
- Waste time and money chasing the wrong hires, deals, or investments.
- Let gut feelings, personal bias, or outside noise dictate decisions.
- Get seduced by shiny objects like a candidate with a $100 million track record, a sales deal that seems like a great opportunity, or an investment everyone else is jumping on.
Instead of being intentional and structured, your process becomes reactive. And before you know it, you are caught in a cycle of misalignment, wasted effort, and frustration.
Why Gut Feelings and Referrals Are The Hiring Kiss of Death
I cannot tell you how many times I’ve heard:
- “My gut will tell me if they are the right hire.”
- “My board member, advisor, or colleague referred them, so they must be great.”
- “They crushed it at [insert impressive company here], so they will crush it for us too.”
Sounds familiar?
The problem with gut instinct is that it is only as good as the data feeding it. If you do not have a clear process to define what good looks like for you, you are basing your decisions on a mix of assumptions, past experiences, and external influence.
And referrals? Just because someone was great for someone else does not mean they are right for your specific business, team, or stage of growth.
Even if they were great before, things change. Context matters. The role, the market, and the business needs are different.
Clarity is the Ultimate Hiring Advantage
The best founders, sellers, and investors do not operate on hope. They make strategic, confident decisions based on a structured process that filters out distractions and keeps them focused on what actually moves the needle.
In my conversation with Stacy, we dug into key strategies that make the difference.
“I’ll Know It When I See It” is a Costly Hiring Process Trap
The idea that you will recognize the right hire, deal, or investment when it is in front of you is a dangerous assumption. Without a clear framework, every new option seems like the best one, leading to endless comparisons, second-guessing, and decision fatigue.
Instead of figuring it out along the way, define success before you even start. Know what you are looking for, why it matters, and how you will measure it.
The Power of a Hiring Scorecard: Stop Winging It
One of the simplest, most effective tools I use with founders is a hiring scorecard. It is not a magic bullet, but it forces clarity upfront.
An effective hiring scorecard defines:
- The critical must-haves for success in the role
- Why each must-have is non-negotiable
- What will not work within those must-haves
- How you will objectively measure candidates against those criteria
This applies beyond hiring. The same principle works in sales and investing. Before stepping into any deal or opportunity, have a framework that defines what success looks like and hold yourself accountable to it.
Avoid the Hiring Shiny Object Syndrome
One of the biggest hiring, sales, and investment pitfalls is getting distracted by surface-level appeal.
- A candidate with a flashy resume but no real alignment with your needs
- A sales deal that looks exciting but is not a real fit for your business model
- An investment that is trending but lacks the fundamentals to deliver long-term value
When you’re clear on your criteria, it is easier to separate signal from noise. You can confidently say yes or no based on fit, not emotion.
The Difference Between a Plan and a Gamble for Hiring
A structured hiring, sales, or investment process is not about rigid checklists, it is about removing ambiguity.
If your process feels like throwing spaghetti at the wall, hoping something sticks, it is time to rethink your approach.
A few questions to ask yourself:
- Do I have a clear definition of what I am looking for?
- Am I evaluating every option against the same criteria?
- Have I built a process that allows me to make decisions with certainty, not guesswork?
If you are relying on hope, gut feel, or outside influence to guide you, you are not operating with clarity. You are gambling.
The Ultimate Hiring Takeaway: Stop Chasing, Start Aligning
If you feel like you are doing more chasing, flying blind, or winging it, it is time to rethink your approach.
The best CEOs, founders, sellers, and investors do not wait for clarity to appear. They create it.
That is exactly what I unpacked with Stacy on Billion Dollar Backstory. We got into the real, no-BS conversation about why hiring, selling, and investing all follow the same rules and how to stop making the same mistakes over and over again.
Run, do not walk, to listen to Episode 84 of Billion Dollar Backstory.
And a BIG thanks to Stacy, not just for trusting me with this conversation, but for being in my world. I am better because of it ❤️
If you’re spending too much time sifting through candidates, unsure of who’s actually right for your business, frustrated by the wasted time interviewing the wrong people, or even worse reeling after the last string of hires didn’t work out… you’re not alone. The good news? There’s a way to fix it. Let’s chat.
